Find Luxury Hotels in Siesta Key, FL

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Check availability on Siesta Key Luxury Hotels

Our top choices for Siesta Key luxury hotels

Deluxe Suite, 2 Bedrooms | Living area | TV
SeaSpray Resort

SeaSpray Resort

4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (74)
"Clean room, incredibly helpful staff. Will be staying here again"
United States
Caleb
The price is ￥38,792
￥43,836 total
includes taxes & fees
Dec 14 - Dec 15
SeaSpray Resort
Condo (LuLu's Key House Leatherback 2/2 Down) | Exterior
Lulu's Key House Leatherback 2/2 Downstairs

Lulu's Key House Leatherback 2/2 Downstairs

4.0 star property
Siesta Key Village
The price is ￥86,985
￥149,097 total
includes taxes & fees
Dec 27 - Dec 28
Lulu's Key House Leatherback 2/2 Downstairs
Condo (House of Sun Siesta Key Crescent Beac) | Exterior
House of The Sun Siesta Key Crescent Beach

House of The Sun Siesta Key Crescent Beach

4.0 star property
South Village
8.0 out of 10, Very Good, (2)
"The area is beautiful. The condo was very nice. Has everything in it. You can cook if you prefer. The Gulf of Mexico was right behind the condo walk out on to the beach. It also has a pool. I have no complains I would def go back again . "
United States
Margaret Theresa
The price is ￥82,935
￥159,200 total
includes taxes & fees
Dec 28 - Dec 29
House of The Sun Siesta Key Crescent Beach
Private beach, white sand, sun loungers, beach umbrellas
The St. Regis Longboat Key Resort

The St. Regis Longboat Key Resort

5.0 star property
Longboat Key
9.8 out of 10, Exceptional, (59)
"Fantastic stay . All servers were great. Staff very friendly and helpful. "
United States
Richard
The price is ￥115,129
￥141,539 total
includes taxes & fees
Dec 14 - Dec 15
The St. Regis Longboat Key Resort
Private beach nearby, white sand, free beach shuttle, beach cabanas
The Ritz-Carlton, Sarasota

The Ritz-Carlton, Sarasota

5.0 star property
Central Sarasota
9.2 out of 10, Wonderful, (1001)
"Great service, comfortable beds"
United States
Richard
The price is ￥85,529
￥106,774 total
includes taxes & fees
Dec 14 - Dec 15
The Ritz-Carlton, Sarasota
Exterior
The Resort at Longboat Key Club

The Resort at Longboat Key Club

4.0 star property
Longboat Key
9.0 out of 10, Wonderful, (689)
"Amazing staff, Sherman the concierge was the absolute best making our experience the greatest it could possibly be! We will be back again and again!"
United States
Jared
The price is ￥69,950
￥86,085 total
includes taxes & fees
Dec 14 - Dec 15
The Resort at Longboat Key Club
Egyptian cotton sheets, premium bedding, in-room safe
Waterline Villas & Marina, Autograph Collection

Waterline Villas & Marina, Autograph Collection

4.0 star property
Holmes Beach
9.6 out of 10, Exceptional, (85)
"Perfect location , villas are great well equipped and very clean, walkable distance to the beach."
United States
Orleys
The price is ￥58,265
￥65,839 total
includes taxes & fees
Dec 17 - Dec 18
Waterline Villas & Marina, Autograph Collection
Poolside bar
Cirque St. Armands Beachside

Cirque St. Armands Beachside

4.0 star property
Lido Key
8.4 out of 10, Very Good, (1005)
"Amazing place "
United States
elvira
The price is ￥43,337
￥55,060 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Cirque St. Armands Beachside
Suite, 1 Bedroom, Pool View | View from room
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4.0 star property
Bradenton
9.4 out of 10, Exceptional, (1879)
"Clean good breakfast nice place"
United States
Sheila
The price is ￥23,703
￥31,186 total
includes taxes & fees
Dec 15 - Dec 16
Compass Hotel by Margaritaville Anna Maria Sound
Outdoor pool, sun loungers
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4.0 star property
Bradenton
9.0 out of 10, Wonderful, (922)
"Great amenities and location. "
United States
Amber
The price is ￥32,823
￥41,492 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Legacy Hotel at IMG Academy
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Siesta Key Hotel Reviews

Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"AC worked great "
barbara 3-night trip
Posted 3 days ago
Tropical Beach Resorts

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Frequently asked questions

Are you searching for the perfect hotel for your luxury getaway to Siesta Key?
Expedia can help you get a flight to Sarasota-Bradenton Intl. Airport (SRQ) airport, and then you can select from a variety of places to stay that will deliver the luxury you seek. Amenities are important when you plan a vacation, so we make it easy to get what you want to make your stay special. If you want an upscale hotel that has fine dining, a spa, or several swimming pools, Expedia can assist you in finding the best luxury hotel experience that Siesta Key offers. Known for its entertainment and live music, Siesta Key also has some interesting things to see and do including Siesta Key Beach, so you may want to take in the local sights during your visit.
When can I expect good weather in Siesta Key?
Planning for the weather is an important factor for making your trip to Siesta Key a success, especially when you're splurging. The hottest months are usually August and July with an average temp of 82°F, while the coldest months are January and February with an average of 66°F. Average annual precipitation for Siesta Key is 44 inches.
What's there to see and do in Siesta Key?
Experience Siesta Key and visit Siesta Key Beach, Crescent Beach, and Siesta Key Marina. If you have a little extra time during your trip, you might want to make a stop at Point of Rocks and Turtle Beach.